Dimethylamine → N,N,2-trimethyl-4-nitrobenzamide

HRID 469826ノート

反応式

HRID 469826 の反応式
[CH3:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].[CH3:14][N:15]1CCOC[CH2:16]1.CCN=C=NCCCN(C)C.Cl.OC1C2N=NNC=2C=CC=1.CNC>ClCCl>[CH3:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([N:15]([CH3:16])[CH3:14])=[O:5]

参加物

7

反応物 5

HCID 674Dimethylamine2 回HCID 79724-Methylmorpholine2 回HCID 747904-Nitro-o-toluic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2 回HCID 178418300HCID 178418300、化合物2 回

生成物 1

HCID 62604610N,N,2-trimethyl-4-nitrobenzamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
40 °C

実験手順

A solution of 2 g (10.7 mmol) 2-methyl-4-nitro-benzoic acid, 1.32 ml (11.8 mmol) N-methyl-morpholine, 2.36 g (12 mmol) EDC-HCl and 2.36 g (12 mmol) HOBt in 50 ml dichloromethane is stirred at RT for 45 min, then dimethylamine solution (5.9 ml, 33% in EtOH) is added and the reaction mixture is heated to 40° C. and stirred at this temperature for 20 h. Another 1.32 ml (11.8 mmol) N-methyl-morpholine, 2.36 g (12 mmol) EDC-HCl and 2.36 g (12 mmol) HOBt (hydroxyl-benzotriazole) are added and stirred for 45 min, the again dimethylamine solution (5.9 ml, 33% in EtOH) is added and the reaction mixture is stirred at 40° C. for 35 h. After that the reaction mixture is cooled to RT and poured onto EtOAc/water. The organic layer is washed with sat. NAHCO3 solution and with water, dried over MgSO4, filtered and the filtrate is concentrated in vacuo. The residue is purified by chromatography (silicagel, hexane:EtOAc=1:1=>EtOAc) to afford the title compound as a yellowish oil.

後処理

  1. stirringstirred for 45 min
  2. stirringthe reaction mixture is stirred at 40° C. for 35 h
  3. temperatureAfter that the reaction mixture is cooled to RT
  4. additionpoured onto EtOAc/water
  5. washThe organic layer is washed with sat. NAHCO3 solution and with water
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationthe filtrate is concentrated in vacuo
  9. customThe residue is purified by chromatography (silicagel, hexane:EtOAc=1:1=>EtOAc)

出典と根拠

ORDレコード
ord-d8cb48903bcf44e6be0d02e4f5871c0f
出典データセット
uspto-grants-2014_01
特許番号
US08629168B2

反応ノート

読み込み中…